3-Aminobenzamide → 2-(3-Carbamoylphenylamino)-2-(4-(2-(3-(3-cyanophenyl)-1-methylureido)ethyl)-3-ethylphenyl)acetic acid

HRID 735602Notes

Reaction equation

HRID 735602 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:26])[N:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][C:16]=2[CH2:24][CH3:25])[CH3:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([NH2:33])=[O:32].O.[C:38]([OH:42])(=[O:41])[CH:39]=O>>[C:31]([C:30]1[CH:29]=[C:28]([NH:27][CH:39]([C:18]2[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][N:11]([CH3:12])[C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=3)=[O:26])=[C:16]([CH2:24][CH3:25])[CH:17]=2)[C:38]([OH:42])=[O:41])[CH:36]=[CH:35][CH:34]=1)(=[O:32])[NH2:33]

Participants

4

Reactant 3

HCID 16453-AminobenzamideHCID 15620607Glyoxylic acid, monohydrateHCID 57842747HCID 57842747, compound

Product 1

HCID 578427832-(3-Carbamoylphenylamino)-2-(4-(2-(3-(3-cyanophenyl)-1-methylureido)ethyl)-3-ethylphenyl)acetic acidYield 37%

Procedure

Using a procedure analogous to that used to prepare 2D, 36E (183 mg, 0.52 mmol) was reacted with 3-aminobenzamide and glyoxylic acid monohydrate to afford 36F (95 mg, 37%) as a yellow film. MS (ESI) m/z 500.3 (M+H)+.

Sources & evidence

ORD record
ord-9bcd5ecb3de74764b9146fd243830e38
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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